Aniline → HCID 21092855, compound

HRID 1785929Notes

Reaction equation

O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[O:13])[C:4]([CH3:23])([CH3:22])[CH2:3]1.I[Si](C)(C)C.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH3:23][C:4]1([CH3:22])[CH2:3][CH:2]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a chilled solution of (4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone (500 mg, 1.6 mmol) in 10 ml dichloromethane was added slowly 0.8 ml iodotrimethylsilane (5.6 mmol) at 0° C. The resulting reaction mixture was stirred at 0° C. for 6 hours. Then the mixture was concentrated under vacuum. The residue was dissolved in 12 ml THF. BaCO3 (630 mg, 3.2 mmol) and aniline (0.17 ml, 1.92 mmol) was added. The mixture was stirred at RT overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexane (1:4) to give (2,2-dimethyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone (150 mg, 24%).

Workup

customThe resulting reaction mixture
concentrationThen the mixture was concentrated under vacuum
dissolutionThe residue was dissolved in 12 ml THF
stirringThe mixture was stirred at RT overnight
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified by silica gel chromatography
washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record: ord-0a31dbd4a1ce4c0f8c119144d42ce7ca
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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